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ADevSecOpsTale of
Business,
Engineering,and
People
@wickett
JamesWickett
Sr. Sec Eng & Dev Advocate @ Verica
Author, LinkedIn Learning
Organizer, DevOps Days Austin, Serverless Days ATX
DevSecOps Days Austin
Author, DevSecOps Handbook (In progress)
@wickett
@wickett
Get the slides now
wickett@verica.io
@wickett
verica.io
An enterprise platform for Continuous Verification,
using Chaos Engineering principles, to take a
proactive and measured approach to preventing
availability and security incidents.
@wickett
ATale ofMoney,
Chaos,andWoe
@wickett
September 15
1896@wickett
William Crush
@wickett
A DevSecOps Tale of Business, Engineering, and People
Wanted promotion
to growbusiness
@wickett
Demolition Derby, but
forTrains
@wickett
1896 introducedthe
ideaofrunningtrain
crashes for Funand
Profit
@wickett
William Crush's
innovationwas
makingthe event
"free"
@wickett
Crushwentfrom
passengeragentto
big-tentpromoter
@wickett
ACityforaDay
Crush,Texas
@wickett
@wickett
Crush,Texas
Population 40,000
@wickett
200 LawOfficersandaJail
Dozenwaterwells
Watertankers
Concessions from Dallas
Preachersand Politicians
Midwaywith Games
@wickett
Biz Model:
Tickets
Concessions
Advertising
@wickett
@wickett
Crushwas
concernedabout
safety
@wickett
@wickett
Engineers evaluated
boilers
Laid 4 miles oftrack
Crowdat200yards
Pressat100yards
@wickett
Word gotout,
Thomas Edison
wantedto film it
@wickett
@wickett
4pm, September 15th,
1896
@wickett
“The rumble ofthetwo
trains, faintand far offat
firstbut growing nearer
and more distinctwith
each fleeting second,was
likethe gathering force ofa
cyclone”
@wickett
@wickett
Thetrains collided
atcombined speed
between 90and 120
mph
@wickett
@wickett
One secondafter
impactthe boilers
exploded
@wickett
@wickett
@wickett
Steam, Iron,Wood
filledthe sky
@wickett
@wickett
Aftermath:
» 4 people died
» Crush fired
» Widespread injuries during incident
» More injuries after incident
» Town shut down
» Lawyers brought in for settlements
@wickett
@wickett
@wickett
Fallout
@wickett
Days later
Crush rehired
Retired from
the MKT 44
years later
@wickett
Demolition Derbyvia
Trains becamea
national
phenomenon
@wickett
But, Inthe hundreds
ofevents post-
Crush,the boilers
held
@wickett
What I learned:
Chronocentrism exists
Engineering is hard
Blame is easy
@wickett
RootCause isaMyth
@wickett
Breaches or Failures
won'tstopbusiness
@wickett
Experimentationand
Learningare Critical
@wickett
DEVSECOPS
@wickett
credit to Josh Zimmerman, the original DevOps Jack Handy
DEVSECOPS
@wickett
First,
Understand DevOps
and howwe got here
@wickett
A DevSecOps Tale of Business, Engineering, and People
Teh Cloud
@wickett
DataSo Big RightNow
@wickett
@wickett
A DevSecOps Tale of Business, Engineering, and People
“DevOps is the inevitable
resultofneedingto do
efficient operations in a
distributed computing
and cloud environment.”
Tom Limoncelli
@wickett
“DevOps is nota
technological
problem. DevOps isa
business problem.”
Damon Edwards
@wickett
DevOps isan
epistemological
breakthroughjoining
disparate peoplearounda
common problem
@wickett
DevOpswas needed
to fixthe inequitable
distribution of
labor
@wickett
10:1
DEV:OPS
@wickett
DevOps isjust
anotherwaypointon
Agile'sjourney
acrossthe business
@wickett
Ok DevOps,that's
fine.
ButwhyDevSecOps?
@wickett
Iasked myselfthis same question
@wickett
@wickett
Securityfinds itselfinthe
same positionthat
operations did inthe
movementofDevOps
@wickett
100:10:1
DEV:OPS:SEC
@wickett
Siloization
@wickett
Security, like ops
strugglesto provide
value in most
organizations
@wickett
“Companiesare
spendingagreatdeal
on security, butwe
read ofmassive
computer-related
attacks. Clearly
something iswrong.
The rootofthe problem
istwofold:we’re
protectingthewrong
things,andwe’re
hurting productivity
inthe process.”
“[Securitybyrisk
assessment]
introducesa
dangerous fallacy:
thatstructured
inadequacyis almost
as good asadequacy
and that underfunded
securityefforts plus
risk managementare
aboutas goodas
properlyfunded
securitywork”
“While engineeringteams
are busy deploying
leading-edgetechnologies,
securityteamsare still
focused on fighting
yesterday’s battles.”
SANS 2018 DevSecOps Survey
@wickett
"manysecurity
teamsworkwitha
worldviewwhere
their goalisto
inhibit change
as muchas possible"
Newtechnology(cloud,
k8s, serverless, ...)and
increased organization
focus on software
deliveryiswhywe need
DevSecOps.
@wickett
A Highly Desireable New Breed:
The DevSecOp
@wickett
...notatool
...notaCI/CD pipeline
...can’tbe bought
@wickett
An inclusive person
participating inthe
movementof
securityinto
devops.
@wickett
DevSecOps Framework:
MEASURE
@wickett
Maker Driven
Experimenting
Automating
SafetyAware
Unrestrained Sharing
Ruggedizing
Empathy
@wickett
MEASURE
@wickett
Maker Driven
@wickett
Weare software engineers
who specialize inaspecific
discipline: security
@wickett
Securitymustbeable to
write code
@wickett
Whyisthis considered
ahottake in our industry?
@wickett
Withallthe
resourcesavailable
today...
@wickett
A DevSecOps Tale of Business, Engineering, and People
Securityis partof
the making
@wickett
Securityalreadyuses DSLs
@wickett
@wickett
The Entire Security
Team Must
Participate in
Software Delivery
@wickett
Empathybuilding
Familiaritywithtools
Ableto move upthe pipeline
@wickett
Abug isabug isabug
@wickett
DefectDensity
studies range
from .5to 10 defects
per KLOC
@wickett
Defectdensity
is never zero
@wickett
With framework/
deps, 500 LOCyou
write can easilybe
400,000 LOC
Hot take:
You cannottrain
developers
towrite secure code
@wickett
Instead, focus on Methods
Developers use
» TDD/BDD/ATDD
» Meaningful comments/commits
» Code Smells, Patterns, Refactoring
» Instrumentation, Observability
@wickett
“The goalshould beto
come upwithasetof
automatedtests that
probeand check
security
configurations and
runtime system
behavior for
securityfeatures
thatwillexecute
everytimethe system
is builtand every
time itis deployed.”
Securityis
connectedwith
quality
@wickett
A DevSecOps Tale of Business, Engineering, and People
A DevSecOps Tale of Business, Engineering, and People
Maker Driven means
» See security as part of engineering
» View quality as a way to bring security in
» Use code, not vendors to solve problems
@wickett
MEASURE
@wickett
Experimenting (and
Learning)
@wickett
Benefitsto Experimentation
» Measured, Repeatable
» Results based on your needs
» Actionable Outcomes
@wickett
“Securityincidents
are not effective
measures ofdetection
becauseatthatpoint
it'salreadytoo late”
Aaron Rinehart
@wickett
A DevSecOps Tale of Business, Engineering, and People
KnowMostLikelyAttacks
and Howto MeasureAbuse
and Misuse
@wickett
“We can'tcede home
fieldadvantage”
Zane Lackey
@wickett
Experimenting necessitates
understanding steadystate
@wickett
Resources
» Shannon Lietz (@devsecops)
» DOES 2018 Talk: youtu.be/yuOuVC8xljw
@wickett
MEASURE
@wickett
Automation
@wickett
A DevSecOps Tale of Business, Engineering, and People
A DevSecOps Tale of Business, Engineering, and People
“Continuous
Deliveryis how
littleyou can
deployatonetime”
Jez Humble & David Farley
@wickett
Optimizetotalcycle
time from code
committo running in
prod
@wickett
15,000deploys in 3.5 years
@wickett
Securityinthe Pipeline
» Software composition analysis
» Lang linters, git-hound, ...
» Scanners, gauntlt
» Monitoring and telemetry
@wickett
“[Deploys] can be
treatedas
standard or
routine changes
thathave been
pre-approved by
management,and
thatdon’trequire
a heavyweight
change review
meeting.”
Resources:
@wickett
linkedin.com/learning/devsecops-building-a-secure-
continuous-delivery-pipeline
@wickett
linkedin.com/learning/devsecops-automated-security-
testing
@wickett
MEASURE
@wickett
SafetyAware
@wickett
Simplevs. Complex Systems
@wickett
Simple Systems:
Linear in nature
Easyto Predict
Ableto comprehend
@wickett
Complex Systems:
Non-linear (bullwhipeffect)
Unpredictable in nature
No mentalmodelavailable
@wickett
Weabstractcomplexity
» Human beings
» Societial issues
» Psychological issues
» Cognitive load
@wickett
Software deals with complexitythrough
abstraction
@wickett
RootCause (inacomplex system)
isaMyth
» Lacks full picture
» Complex systems are not linear
» Result of blame culture
» Forgets organizational decisions
» Puts the focus on the event over situation
@wickett
“Drifting into failure is
a gradual, incremental
decline into disaster
driven by
environmental
pressure, unruly
technologyand social
proccessesthat
normalize growing
risk. No organization is
exempt from drifting
into failure”
@wickett
Boeing 737Max
» Maneuvering Characteristics Augmentation System
(MCAS)
» MCAS commands the trim without notifying the
pilots
» This is software
@wickett
Softwarewas
fightingthe pilots
silently
@wickett
High-speed decision
making inan up-
tempo environment
@wickett
Software is eating theworld
@wickett
“The growth of
complexityin
societyhas got
ahead ofour
understaindin
g of how
complex
systemswork
and fail”
@wickett
@wickett
Operationsand
Security's burdento
rationalize system
models
@wickett
“Failures are a
systems problem
because there is not
enough safety
margin. ”
@adrianco
@wickett
“Failure isan
inevitable by-
productofa
complex
system's
normal
functioning”
Where SecurityFits
» Add safety margin
» Telemetry and instrumentation
» Blameless retros
» ...more to explore in this area
@wickett
Resources
» Drift into Failure by Dekker
» Understanding Human Error Video Series youtu.be/
Fw3SwEXc3PU
» @jpaulreed coverage of Boeing medium.com/
@jpaulreed
» Richard Cook paper bit.ly/2ydDQS2
@wickett
MEASURE
@wickett
Unrestrained
Sharing
@wickett
“Culture isthe most
importantaspectto
devops succeeding
inthe enterprise”
Patrick DeBois
@wickett
DevSecOps isthe
extension ofthe
DevOps culture for
the inclusion of
Security
@wickett
“Asecurityteamwho
embraces openness
aboutwhatitdoes
and why, spreads
understanding.”
Rich Smith
@wickett
Unrestrained Sharing
affects culture
@wickett
Unrestrained
Sharing goes
againstsecurity's
standard operating
procedure
@wickett
Itwillfeel
uncomfortable
@wickett
Sharing breaks
down silos
@wickett
Four Keysto Culture
» Mutual Understanding
» Shared Language
» Shared Views
» Collaborative Tooling
@wickett
20% ofdevelopers
don'tknowwhat
securityexpects of
them
@wickett
SecuritySharesThrough
» Making invisible as visible
» Security Observability
» APIs, webhooks, dev tooling
@wickett
This includes the
auditors
@wickett
A DevSecOps Tale of Business, Engineering, and People
Resources
» Phoenix Project
» Agile Application Security
» dearauditor.org
@wickett
MEASURE
@wickett
Ruggedization
@wickett
@wickett
Software BillofMaterials
Knowwhatyou have
@wickett
Favor ShortLived Systems
Cattle notPets
@wickett
DIE Framework
Distributed
Immutable
Ephemeral
source: @sounilyu
@wickett
Ruggedization in 2020
1. Deception
2. Chaos Engineering
@wickett
Deception
» Honeypots, Tarpits, Mantraps
» Simple to get started (http headers)
» HoneyPy, DeceptionLogic
@wickett
“We’re moving from
disaster recovery
to chaos engineering
to resiliency”
@adrianco
@wickett
“[Chaos Engineering is]
empiricalratherthan formal.
We don’tuse modelsto
understandwhatthe system
should do.We run experiments
to learnwhat itdoes.”
Michael Nygard, Release It 2nd Ed.
@wickett
“The security discipline of
[chaos] experimentation is
done in orderto build
confidence inthe system’s
abilityto defend against
malicious conditions.”
Aaron Rinehart
@wickett
Chaos Engineering
» Experiments that span eng and security
» Manual opt-out
» Valuable Learning
» Controlled experiment blast radius
@wickett
Resources
» Aaron Rinehart's talk at RSA youtu.be/wLlME4Ve1go
» principlesofchaos.org
» Release It! 2nd ed., Nygard
» Phillip Maddux's talk: youtu.be/k81xKjCEeqE
» Herb Todd's talk: youtu.be/Cf_XXmRLnRQ
@wickett
MEASURE
@wickett
Empathy
@wickett
A DevSecOps Tale of Business, Engineering, and People
“those stupid
developers”
Security
@wickett
“youwantamachine
powered offand
unplugged”
Developer
@wickett
Halfofdevelopers
saythatdon'thave
enoughtimeto spend
on security
Don’tbeablocker
be an enabler
@wickett
Maker Driven
Experimenting
Automating
SafetyAware
Unrestrained Sharing
Ruggedizing
Empathy
@wickett
Share your story
book@devsecops.org
@wickett
Get the slides
wickett@verica.io
Questions
@wickett
@wickett

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A DevSecOps Tale of Business, Engineering, and People